Triple the Taxes. Zero The Fun

Triple the Taxes. Zero The Fun

Because of my father’s passing, I was given the joy of filing not just our family’s 1040, but also my father’s. Now my father, even more so than me, was always ready for tax season. He had a binder with everything, and I had his computer with his previous year’s return. After sitting down, I felt confident that I could get it done.

I was originally willing to work with a CPA, but my Dad did his own taxes and taught me to do mine. I remember him going to the library, getting the paper forms, and doing all the math by hand before TurboTax existed. Also, when I called the accounting firm, they said they would call me back…

Our individual taxes were fairly straightforward. We did not have the new required IRA distribution yet, so it was very similar to 2024.

However, we now had the new joy of estate taxes.

My family’s estate is simpler than many, I’m sure. My mother passed away years ago, and my Dad’s home was in a Family Trust. He had one retirement account, one investment account, and two checking accounts. No other real estate, one car, and some simple belongings in the house.

In 2018, there was a large increase to the federal estate tax exemption, and in 2026, as long as the estate is under $16 million, you do not need to file Form 706.

But the fun doesn’t stop with the federal government. You need to check the state where your relative lived and see whether it has an estate or inheritance tax. Most states don’t. Illinois does.

Remember, estate tax is calculated on the entire estate: the value of the home, retirement accounts, and everything they owned when they passed away. Once they pass, there is nothing that can be done. You can’t move funds around or shelter assets. The estate is the estate.

Illinois gives you the honor of filling out Form 700 and Form 706. You then get to use a website to calculate the amount of money you owe. That’s right. The way Illinois calculates estate taxes is too complicated to reasonably do by hand.

Also, Illinois made changes to its estate taxes in 2026. So now it is much simpler, and cheaper, to die in Illinois. Unfortunately, my Dad passed away in 2025, so I still had to deal with the old pain.

I started working on the forms and was surprised by how straightforward everything was. I did need to work with Fidelity to get some additional documents because you need the exact value on the date of death. You can’t just use the end-of-the-month statements, for example.

The bill was steep.

I realized that I finally needed a CPA. I had already done everything I thought I could and paid the estimated tax bill, but I wanted to make sure I was at least in the right ballpark.

I filed an extension for the paperwork, which allowed me to delay filing until November. If I hadn’t paid the taxes by May, I would have received extreme penalties. If your payment is more than a month late, you owe an additional 10% penalty.

Just handing everything over to the CPA was a huge weight off my shoulders. But then I waited three weeks and heard nothing. All I was expecting was a couple of hours of review.

Those weeks turned into months, and I finally gave up on CPAs and turned to a local estate lawyer. Based on her website, she seemed to focus on the financial side of estates and specifically mentioned estate taxes.

Her assistant asked who I was currently working with. I was surprised she assumed I already had someone, and she seemed equally surprised when I told her I wasn’t working with anyone. I have to assume it was because I was asking detailed questions about Form 700.

It was now the middle of August. A full year since my father had passed. I was embarrassed that this still hadn’t been taken care of. Their first opening wasn’t until early September, but it felt like the best path forward.

I sent them my PDF of forms weeks and supporting documentation so they could review them before our meeting. I was shaking in the waiting room. I was ready for the lawyer to tell me that I had done multiple things wrong, both in the process and on the forms.

She sat down with a notepad full of items to discuss. The first was that I had two documents with different numbers. I told her that was my fault because I had done an estimate and forgotten to update one of the documents. She then pointed out that there were two boxes I should have marked “Yes” instead of “No.”

I was confused about why she was starting with these relatively minor issues, but I was still waiting for the bomb to drop. She then said I needed to add the kids’ names to the inheritance list because they had UTMAs. After that, she just kind of looked at me, and I said, “Oh… so that’s it?” She said, “Yeah. Just mail everything in with the documentation.”

She didn’t even ask her team to review it again or send it to a CPA. She told me she had assistants who didn’t do as well as I did on their first attempt. My confidence shot up, and I quickly realized that I was finally going to be done with my father’s estate taxes.

All that was left was double-checking the math, printing everything, making copies, mailing it in, paying the remaining taxes, and finally emptying the bank accounts to my brother and me.

The lawyer told me the state is currently 12–18 months behind on reviewing estate tax filings. So there isn’t much else to do now except hope I did everything correctly.

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